Benzoyl chloride → HCID 769456, compound

HRID 1200157Notes

Reaction equation

HRID 1200157 reaction equation
[S:1]1[CH2:5][C@@H:4]([C:6]([OH:8])=[O:7])[NH:3][CH2:2]1.[OH-].[Na+].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:11]([N:3]1[C@H:4]([C:6]([OH:8])=[O:7])[CH2:5][S:1][CH2:2]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 93176L-Thioproline

Product 1

HCID 769456HCID 769456, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1 liter of acetone was added to a solution of 266.2 g of (4R)-thiazolidine-4-carboxylic acid in 1 liter of a 2N aqueous solution of sodium hydroxide. The solution was cooled at a temperature between 2° and 5° C., and then a solution of 280 g of benzoyl chloride in 0.8 liter of acetone was added dropwise, while maintaining the pH value of the reaction mixture at 7.5-8.0 by the addition of 1 liter of a 2N aqueous solution of sodium hydroxide. When the addition was complete, the reaction mixture was stirred at a temperature between 0° and 5° C. for 1 hour, after which it was concentrated by evaporation under reduced pressure to a volume of about 2.5 liters. The concentrate was washed with 2 liters of ethyl acetate, the aqueous phase was adjusted to a pH value of 2.0 by the addition of concentrated hydrochloric acid, maintaining the temperature at between 0° and 5° C., and the mixture was extracted twice, each time with 2 liters of ethyl acetate. The ethyl acetate phase was washed with a 10% w/v aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then distilled off to give 511.2 g of (4R)-3-benzoylthiazolidine-4-carboxylic acid.

Workup

  1. temperatureThe solution was cooled at a temperature between 2° and 5° C.
  2. temperaturewhile maintaining the pH value of the reaction mixture at 7.5-8.0
  3. additionWhen the addition
  4. concentrationafter which it was concentrated by evaporation under reduced pressure to a volume of about 2.5 liters
  5. washThe concentrate was washed with 2 liters of ethyl acetate
  6. additionthe aqueous phase was adjusted to a pH value of 2.0 by the addition of concentrated hydrochloric acid
  7. temperaturemaintaining the temperature at between 0° and 5° C.
  8. extractionthe mixture was extracted twice
  9. washThe ethyl acetate phase was washed with a 10% w/v aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-3e76e8182747412f845a49b83e82b05b
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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